Triethylamine → HCID 57709023, compound

HRID 546947Notes

Reaction equation

HRID 546947 reaction equation
C(N(CC)CC)C.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].CN(C1C=CC=CN=1)C.[CH2:25]([C:27]([C:46]1[CH:51]=[CH:50][C:49](/[CH:52]=[CH:53]/[C:54]([C:60]([F:63])([F:62])[F:61])([OH:59])[C:55]([F:58])([F:57])[F:56])=[C:48]([CH3:64])[CH:47]=1)([C:30]1[CH:35]=[CH:34][C:33]([B:36]2[O:40][C:39]([CH3:42])([CH3:41])[C:38]([CH3:44])([CH3:43])[O:37]2)=[C:32]([CH3:45])[CH:31]=1)[CH2:28][CH3:29])[CH3:26]>CN(C)C=O.O>[C:11]([Si:8]([CH3:10])([CH3:9])[O:59][C:54]([C:60]([F:63])([F:62])[F:61])([C:55]([F:56])([F:57])[F:58])/[CH:53]=[CH:52]/[C:49]1[CH:50]=[CH:51][C:46]([C:27]([C:30]2[CH:35]=[CH:34][C:33]([B:36]3[O:40][C:39]([CH3:41])([CH3:42])[C:38]([CH3:44])([CH3:43])[O:37]3)=[C:32]([CH3:45])[CH:31]=2)([CH2:25][CH3:26])[CH2:28][CH3:29])=[CH:47][C:48]=1[CH3:64])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 57708964(E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol

Product 1

HCID 57709023HCID 57709023, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.10 mL, 0.72 mmol), t-butyldimethylsilyl chloride (48.5 mg, 0.322 mmol) and dimethylaminopyridine (1 mg, 0.008 mmol) were added to a solution of (E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol (Example 26-(5); 47.0 mg, 0.082 mmol) in N,N-dimethylformamide (0.10 mL), and the mixture was stirred at room temperature for 24 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=50/1) to give the title compound (47 mg, 84%).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-3280dce026594dd4a63d3b7fbade8e15
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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